CA1297123C - Methode pour la cosynthese d'ethyleneglycol et de carbonate de dimethyle - Google Patents

Methode pour la cosynthese d'ethyleneglycol et de carbonate de dimethyle

Info

Publication number: CA1297123C
Authority: CA; Canada
Prior art keywords: zirconium; methanol; titanium; carbonate; tin
Prior art date: 1986-07-31
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA000532588A

Other languages

English (en)

Inventor

John Frederick Knifton

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Texaco Development Corp

Original Assignee

Texaco Development Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-07-31

Filing date

1987-03-20

Publication date

1992-03-10

1987-03-20 Application filed by Texaco Development Corp filed Critical Texaco Development Corp

1992-03-10 Application granted granted Critical

1992-03-10 Publication of CA1297123C publication Critical patent/CA1297123C/fr

2009-03-10 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 109
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 title claims abstract description 38
238000000034 method Methods 0.000 title claims abstract description 38
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 169
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims abstract description 55
229910052726 zirconium Inorganic materials 0.000 claims abstract description 22
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims abstract description 21
239000010936 titanium Substances 0.000 claims abstract description 17
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 16
229910052719 titanium Inorganic materials 0.000 claims abstract description 16
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 6
-1 zirconium alkoxides Chemical class 0.000 claims description 20
239000002815 homogeneous catalyst Substances 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
YOBOXHGSEJBUPB-MTOQALJVSA-N (z)-4-hydroxypent-3-en-2-one;zirconium Chemical compound [Zr].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O YOBOXHGSEJBUPB-MTOQALJVSA-N 0.000 claims description 8
VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 6
239000002638 heterogeneous catalyst Substances 0.000 claims description 6
150000003754 zirconium Chemical class 0.000 claims description 5
229910001928 zirconium oxide Inorganic materials 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 4
RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical group [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 claims description 4
229910052718 tin Chemical class 0.000 claims description 3
RYSXWUYLAWPLES-MTOQALJVSA-N (Z)-4-hydroxypent-3-en-2-one titanium Chemical compound [Ti].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RYSXWUYLAWPLES-MTOQALJVSA-N 0.000 claims description 2
208000036366 Sensation of pressure Diseases 0.000 claims description 2
GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 claims description 2
JJLKTTCRRLHVGL-UHFFFAOYSA-L [acetyloxy(dibutyl)stannyl] acetate Chemical compound CC([O-])=O.CC([O-])=O.CCCC[Sn+2]CCCC JJLKTTCRRLHVGL-UHFFFAOYSA-L 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
ZEIWWVGGEOHESL-UHFFFAOYSA-N methanol;titanium Chemical compound [Ti].OC.OC.OC.OC ZEIWWVGGEOHESL-UHFFFAOYSA-N 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
ZGSOBQAJAUGRBK-UHFFFAOYSA-N propan-2-olate;zirconium(4+) Chemical compound [Zr+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-] ZGSOBQAJAUGRBK-UHFFFAOYSA-N 0.000 claims description 2
TWRYZRQZQIBEIE-UHFFFAOYSA-N tetramethoxystannane Chemical compound [Sn+4].[O-]C.[O-]C.[O-]C.[O-]C TWRYZRQZQIBEIE-UHFFFAOYSA-N 0.000 claims description 2
150000003755 zirconium compounds Chemical group 0.000 claims description 2
DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 claims description 2
ZUWXYYNYQIKFSJ-UHFFFAOYSA-N zirconium(2+);dinitrate Chemical compound [Zr+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZUWXYYNYQIKFSJ-UHFFFAOYSA-N 0.000 claims description 2
229940093476 ethylene glycol Drugs 0.000 claims 4
229910021626 Tin(II) chloride Inorganic materials 0.000 claims 1
PLONEVHFXDFSLA-UHFFFAOYSA-N ethyl hexanoate;tin(2+) Chemical compound [Sn+2].CCCCCC(=O)OCC PLONEVHFXDFSLA-UHFFFAOYSA-N 0.000 claims 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 claims 1
KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims 1
239000003054 catalyst Substances 0.000 abstract description 15
239000000203 mixture Substances 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 11
238000005809 transesterification reaction Methods 0.000 description 10
239000007788 liquid Substances 0.000 description 8
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000012018 catalyst precursor Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
BNUFVLQIPHELMH-UHFFFAOYSA-N 1,3-dioxolan-2-one;methanol Chemical compound OC.O=C1OCCO1 BNUFVLQIPHELMH-UHFFFAOYSA-N 0.000 description 4
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
150000004649 carbonic acid derivatives Chemical class 0.000 description 4
239000012263 liquid product Substances 0.000 description 4
150000000180 1,2-diols Chemical class 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
BOZRCGLDOHDZBP-UHFFFAOYSA-N 2-ethylhexanoic acid;tin Chemical compound [Sn].CCCCC(CC)C(O)=O BOZRCGLDOHDZBP-UHFFFAOYSA-N 0.000 description 2
BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
239000005977 Ethylene Substances 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
150000001339 alkali metal compounds Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000005910 alkyl carbonate group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
150000005676 cyclic carbonates Chemical class 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000008188 pellet Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000012974 tin catalyst Substances 0.000 description 2
150000003606 tin compounds Chemical class 0.000 description 2
229910001887 tin oxide Inorganic materials 0.000 description 2
QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 2
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 2
OERNJTNJEZOPIA-UHFFFAOYSA-N zirconium nitrate Chemical compound [Zr+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O OERNJTNJEZOPIA-UHFFFAOYSA-N 0.000 description 2
ZXAUZSQITFJWPS-UHFFFAOYSA-J zirconium(4+);disulfate Chemical compound [Zr+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZXAUZSQITFJWPS-UHFFFAOYSA-J 0.000 description 2
LSWWNKUULMMMIL-UHFFFAOYSA-J zirconium(iv) bromide Chemical compound Br[Zr](Br)(Br)Br LSWWNKUULMMMIL-UHFFFAOYSA-J 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
HTWIZMNMTWYQRN-UHFFFAOYSA-N 2-methyl-1,3-dioxolane Chemical compound CC1OCCO1 HTWIZMNMTWYQRN-UHFFFAOYSA-N 0.000 description 1
DUFCMRCMPHIFTR-UHFFFAOYSA-N 5-(dimethylsulfamoyl)-2-methylfuran-3-carboxylic acid Chemical compound CN(C)S(=O)(=O)C1=CC(C(O)=O)=C(C)O1 DUFCMRCMPHIFTR-UHFFFAOYSA-N 0.000 description 1
SZRVNOQINZUPBH-UHFFFAOYSA-M CC([O-])C.[Ti].C(C)C(C(=O)[O-])CCCC.[Sn+2] Chemical compound CC([O-])C.[Ti].C(C)C(C(=O)[O-])CCCC.[Sn+2] SZRVNOQINZUPBH-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
239000004606 Fillers/Extenders Substances 0.000 description 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
229910008159 Zr(SO4)2 Inorganic materials 0.000 description 1
229910007938 ZrBr4 Inorganic materials 0.000 description 1
229910026551 ZrC Inorganic materials 0.000 description 1
229910008334 ZrO(NO3)2 Inorganic materials 0.000 description 1
OTCHGXYCWNXDOA-UHFFFAOYSA-N [C].[Zr] Chemical compound [C].[Zr] OTCHGXYCWNXDOA-UHFFFAOYSA-N 0.000 description 1
INNSZZHSFSFSGS-UHFFFAOYSA-N acetic acid;titanium Chemical compound [Ti].CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O INNSZZHSFSFSGS-UHFFFAOYSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001508 alkali metal halide Inorganic materials 0.000 description 1
150000008045 alkali metal halides Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000001502 aryl halides Chemical class 0.000 description 1
235000015241 bacon Nutrition 0.000 description 1
239000002585 base Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
WZRZKFUVOSDSBQ-UHFFFAOYSA-N butane-1,2-diol;carbonic acid Chemical compound OC(O)=O.CCC(O)CO WZRZKFUVOSDSBQ-UHFFFAOYSA-N 0.000 description 1
150000005323 carbonate salts Chemical class 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
229940000425 combination drug Drugs 0.000 description 1
AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
KLGVAUJELUIWKZ-UHFFFAOYSA-N dimethyl carbonate;ethane-1,2-diol Chemical compound OCCO.COC(=O)OC KLGVAUJELUIWKZ-UHFFFAOYSA-N 0.000 description 1
PWEVMPIIOJUPRI-UHFFFAOYSA-N dimethyltin Chemical class C[Sn]C PWEVMPIIOJUPRI-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
UARGAUQGVANXCB-UHFFFAOYSA-N ethanol;zirconium Chemical compound [Zr].CCO.CCO.CCO.CCO UARGAUQGVANXCB-UHFFFAOYSA-N 0.000 description 1
238000004508 fractional distillation Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
238000001030 gas--liquid chromatography Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
IKGXNCHYONXJSM-UHFFFAOYSA-N methanolate;zirconium(4+) Chemical compound [Zr+4].[O-]C.[O-]C.[O-]C.[O-]C IKGXNCHYONXJSM-UHFFFAOYSA-N 0.000 description 1
UJVRJBAUJYZFIX-UHFFFAOYSA-N nitric acid;oxozirconium Chemical compound [Zr]=O.O[N+]([O-])=O.O[N+]([O-])=O UJVRJBAUJYZFIX-UHFFFAOYSA-N 0.000 description 1
YTEWOCYAXODONQ-UHFFFAOYSA-N oxygen(2-) zirconium(3+) nitrate Chemical compound [O-2].[Zr+3].[N+](=O)([O-])[O-] YTEWOCYAXODONQ-UHFFFAOYSA-N 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
229910052716 thallium Inorganic materials 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
150000003476 thallium compounds Chemical class 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
231100000925 very toxic Toxicity 0.000 description 1
ZVWKZXLXHLZXLS-UHFFFAOYSA-N zirconium nitride Chemical compound [Zr]#N ZVWKZXLXHLZXLS-UHFFFAOYSA-N 0.000 description 1
OMQSJNWFFJOIMO-UHFFFAOYSA-J zirconium tetrafluoride Chemical compound F[Zr](F)(F)F OMQSJNWFFJOIMO-UHFFFAOYSA-J 0.000 description 1
XLMQAUWIRARSJG-UHFFFAOYSA-J zirconium(iv) iodide Chemical compound [Zr+4].[I-].[I-].[I-].[I-] XLMQAUWIRARSJG-UHFFFAOYSA-J 0.000 description 1
GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/128—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by alcoholysis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
- C07C68/065—Preparation of esters of carbonic or haloformic acids from organic carbonates from alkylene carbonates
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Catalysts (AREA)

CA000532588A 1986-07-31 1987-03-20 Methode pour la cosynthese d'ethyleneglycol et de carbonate de dimethyle Expired - Fee Related CA1297123C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US891,093		1986-07-31
US06/891,093 US4661609A (en)	1986-07-31	1986-07-31	Process for cosynthesis of ethylene glycol and dimethyl carbonate

Publications (1)

Publication Number	Publication Date
CA1297123C true CA1297123C (fr)	1992-03-10

Family

ID=25397604

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000532588A Expired - Fee Related CA1297123C (fr)	1986-07-31	1987-03-20	Methode pour la cosynthese d'ethyleneglycol et de carbonate de dimethyle

Country Status (5)

Country	Link
US (1)	US4661609A (fr)
EP (1)	EP0255252B1 (fr)
JP (1)	JPS6341432A (fr)
CA (1)	CA1297123C (fr)
DE (1)	DE3781742T2 (fr)

Families Citing this family (41)

* Cited by examiner, † Cited by third party
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DE4105554A1 (de) *	1991-02-22	1992-08-27	Bayer Ag	Verfahren zur herstellung von dialkylcarbonaten
JP2631803B2 (ja) *	1992-11-25	1997-07-16	株式会社日本触媒	ジアルキルカーボネートの製造方法
US6594688B2 (en) *	1993-10-01	2003-07-15	Collaboration Properties, Inc.	Dedicated echo canceler for a workstation
US5489703A (en) *	1995-05-19	1996-02-06	Amoco Corporation	Reaction extraction of alkyl carbonate
EP1086940B1 (fr) *	1998-06-10	2007-05-02	Asahi Kasei Chemicals Corporation	Procede de production continue de diol et de carbonate dialcoyle
US6365767B1 (en)	1999-05-28	2002-04-02	Exxonmobil Chemical Patents Inc.	Process for co-production of dialkyl carbonate and alkanediol
US6207850B1 (en)	1999-11-03	2001-03-27	Mobil Oil Corporation	Process for co-production of dialkyl carbonate and alkanediol
US6407279B1 (en)	1999-11-19	2002-06-18	Exxonmobil Chemical Patents Inc.	Integrated process for preparing dialkyl carbonates and diols
US6162940A (en) *	1999-12-14	2000-12-19	Mobil Oil Corporation	Process for co-production of dialkyl carbonate and alkanediol
JP3659109B2 (ja) *	2000-01-19	2005-06-15	三菱化学株式会社	エチレングリコールと炭酸エステルの併産方法
US6342623B1 (en)	2000-02-04	2002-01-29	Exxonmobil Chemical Patents Inc.	Process for co-production of dialkyl carbonate and alkanediol
US6166240A (en) *	2000-02-22	2000-12-26	Mobil Oil Corporation	Process for co-production of dialkyl carbonate and alkanediol
UA76478C2 (uk) *	2001-07-09	2006-08-15	Лонза Інк.	Способи одержання алкілкарбонатів четвертинного амонію in situ
US6573396B2 (en)	2001-10-12	2003-06-03	Exxonmobil Chemical Patents Inc.	Co-production of dialkyl carbonates and diols with treatment of hydroxy alkyl carbonate
US6620959B1 (en) *	2002-04-16	2003-09-16	Exxonmobil Chemical Patents Inc.	Process for the production of unsymmetric and/or symmetric dialkyl carbonates and diols
WO2005123638A1 (fr) *	2004-06-17	2005-12-29	Asahi Kasei Chemicals Corporation	Procédé servant à produire un carbonate de dialkyle et un diol
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IT1396959B1 (it)	2009-12-18	2012-12-20	Eni Spa	Composizione di gasolio comprendente biodiesel e dietil carbonato da bioetanolo
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1986
- 1986-07-31 US US06/891,093 patent/US4661609A/en not_active Expired - Fee Related
1987
- 1987-03-20 CA CA000532588A patent/CA1297123C/fr not_active Expired - Fee Related
- 1987-07-08 DE DE8787306054T patent/DE3781742T2/de not_active Expired - Fee Related
- 1987-07-08 EP EP87306054A patent/EP0255252B1/fr not_active Expired - Lifetime
- 1987-07-22 JP JP62181292A patent/JPS6341432A/ja active Pending

Also Published As

Publication number	Publication date
JPS6341432A (ja)	1988-02-22
EP0255252A2 (fr)	1988-02-03
EP0255252B1 (fr)	1992-09-16
US4661609A (en)	1987-04-28
DE3781742T2 (de)	1993-03-18
DE3781742D1 (de)	1992-10-22
EP0255252A3 (en)	1989-02-15

Legal Events

Date	Code	Title	Description
1996-09-10	MKLA	Lapsed

Publication	Publication Date	Title
US4661609A (en)	1987-04-28	Process for cosynthesis of ethylene glycol and dimethyl carbonate
US4181676A (en)	1980-01-01	Process for the preparation of dialkyl carbonates
US6573396B2 (en)	2003-06-03	Co-production of dialkyl carbonates and diols with treatment of hydroxy alkyl carbonate
US4691041A (en)	1987-09-01	Process for production of ethylene glycol and dimethyl carbonate
US4307032A (en)	1981-12-22	Process for the preparation of dialkyl carbonates
EP1112120B1 (fr)	2004-10-20	Procede et catalyseur pour la fabrication de carbonates dedialkyle
US6620959B1 (en)	2003-09-16	Process for the production of unsymmetric and/or symmetric dialkyl carbonates and diols
EP0638541A1 (fr)	1995-02-15	Procédé de production du carbonate de dialkyle
EP2121565B1 (fr)	2012-11-28	Procédé de préparation d'un alcanediol et d'un carbonate de dialkyle
KR100899058B1 (ko)	2009-05-25	디알킬 카보네이트의 제조 방법
US4734518A (en)	1988-03-29	Process for cosynthesis of ethylene glycol and dimethyl carbonate
US7279592B2 (en)	2007-10-09	Process for making dialkyl carbonates
US6166240A (en)	2000-12-26	Process for co-production of dialkyl carbonate and alkanediol
US5214182A (en)	1993-05-25	Process for cogeneration of ethylene glycol and dimethyl carbonate
US4734525A (en)	1988-03-29	Process for the production of formates
US5206408A (en)	1993-04-27	Process for the preparation of unsymmetric dialkyl carbonates
EP2279163B1 (fr)	2014-05-21	Procédé de préparation d'un alcanédiol et d'un carbonate de dialkyle
WO2001056971A1 (fr)	2001-08-09	Procede pour la coproduction de carbonate de dialkyle et d'alcanediol
JPH07330686A (ja)	1995-12-19	ジアルキルカーボネートの製造方法
JP3363517B2 (ja)	2003-01-08	ジアルキルカーボネートとグリコールの同時製造方法
US7598410B2 (en)	2009-10-06	Method for the production of organic carbonates
GB1579896A (en)	1980-11-26	Manufacture of glycol esters and glycols
JPH0873411A (ja)	1996-03-19	ジアルキルカーボネートの製造方法
WO2021110627A1 (fr)	2021-06-10	Procédé pour l'élimination d'une impureté d'alcanol éther à partir d'un flux de carbonate organique
JPH01311054A (ja)	1989-12-15	炭酸ジアルキルの製造方法